Hydrochloric Acid → 4-Cyclopropylaniline

HRID 1898333Notes

Reaction equation

HRID 1898333 reaction equation
[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([N+:10]([O-])=O)=[CH:6][CH:5]=2)[CH2:3][CH2:2]1.Cl>[Fe].CO>[CH:1]1([C:4]2[CH:9]=[CH:8][C:7]([NH2:10])=[CH:6][CH:5]=2)[CH2:3][CH2:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 3127131-Cyclopropyl-4-nitrobenzene

Product 1

HCID 122539274-CyclopropylanilineYield 553.4%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 887MethanolSolvent

Procedure

The title compound was prepared following the procedure described for Step-9 of Intermediate-1 using 1-cyclopropyl-4-nitrobenzene (0.400 g, 0.407 mmol), methanol (10 mL), iron powder (catalytic amount) and conc. HCl (0.5 mL) to afford 0.300 g of the desired product. 1HNMR (DMSO-d6): δ 0.43-0.48 (m, 2H), 0.74-0.80 (m, 2H), 1.23-1.74 (m, 1H), 4.79 (s, 2H), 6.44 (d, J=8.1 Hz, 2H), 6.73 (d, J=8.1 Hz, 2H); [M+H]+: 134.20.

Workup

  1. customThe title compound was prepared

Sources & evidence

ORD record
ord-6200688894fa480bbbfd8f766e277357
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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